Orlando to Chicago (SFB–MDW) — Airlines, Schedules & Connections

SFB Airport Page →
airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 17 1-stop flights
No nonstop service between SFB and MDW. Nearest airports to SFB with scheduled service: Orlando International Airport (MCO, 24 mi) · Tampa International Airport (TPA, 96 mi) · Jacksonville International Airport (JAX, 122 mi)
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 10 hubs
BNA Nashville 4h 19m G4LXJ → WN Nashville (BNA) to Chicago flights
TYS Knoxville/Maryville 4h 31m G4 → G4 Knoxville/Maryville (TYS) to Chicago flights
CVG Cincinnati / Covington 4h 44m G4 → WN Cincinnati / Covington (CVG) to Chicago flights
AVL Asheville 5h 4m G4 → G4 Asheville (AVL) to Chicago flights
PIT Pittsburgh 5h 41m G4 → WN Pittsburgh (PIT) to Chicago flights
OMA Omaha 5h 43m G4 → JTLWN Omaha (OMA) to Chicago flights
ALB Albany 5h 46m G4 → WN Albany (ALB) to Chicago flights
OKC Oklahoma City 5h 48m G4 → WN Oklahoma City (OKC) to Chicago flights
GRR Grand Rapids 5h 59m G4 → WN Grand Rapids (GRR) to Chicago flights
DSM Des Moines 6h 3m G4 → EJAWN Des Moines (DSM) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Orlando to Chicago
Connecting service available through multiple hubs.
-1h behind

While no nonstop service exists between SFB and MDW, 1-stop connecting options are available.

Also explore SFB Routes MDW Routes SFB Live Flights MDW Live Flights SFB Delays MDW Delays
All flights from Chicago (MDW) Chicago to Orlando flights
Connections

Connection Landscape

1-stop and 2-stop options for SFB to MDW.
1-STOP
One-Stop Connections
17
Hubs
~4h
Fastest
~31h
Longest
BNA ~4h 19m TYS ~4h 31m CVG ~4h 44m AVL ~5h 4m PIT ~5h 41m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
892
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
SFB → MDW
0%
Frequent delays expected. Consider flexible booking.
Departing
0%
Arriving
65%
Return
MDW → SFB
64%
Moderate delays possible. Allow buffer time.
Departing
64%
Arriving
60%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. SFB delays → MDW delays →
Alternatives

Other ways to reach Chicago from Orlando

Nearby airports with service to Chicago Midway International Airport.
Metric SFB→MDW MCO→MDW LAL→MDW
Distance from SFB – 24 mi 72 mi
Nonstop airlines – 7 1
Weekly flights – 101 –
Departure OTP 0% – –
Orlando (MCO) to Chicago flights · Lakeland (LAL) to Chicago flights · St Augustine (UST) to Chicago flights
Airports within 200 miles of SFB with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind Orlando.
SFB: EDT · MDW: CDT

When it's 6:00 PM in Orlando, it's 5:00 PM in Chicago.
Facts

SFB–MDW Quick Facts

Key statistics for the Orlando to Chicago route.
Route details
Time difference-1 hour
Airlines (nonstop)0
1-stop connectionsAvailable
Origin: SFB
Full nameOrlando Sanford International Airport
IATA / ICAOSFB / KSFB
TimezoneAmerica/New_York
Passengers/yr2.8M
Elevation55 ft / 17 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about SFB to MDW flights.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Nashville, McGhee Tyson and Cincinnati Northern Kentucky.
Chicago is 1 hour behind Orlando.
Yes, return flights from MDW to SFB are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include MCO, LAL and UST. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Nashville, McGhee Tyson and Cincinnati Northern Kentucky. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and St Augustine (UST).